5 Best Music Videos Featuring Crossdressing

January 25, 2018

Recently, Pink released her latest music video Beautiful Trauma. Over here at Glamour Boutique, we haven’t been able to get enough of the pop icons newest video for one main reason – getting to see Channing Tatum crossdress. The video shows Pink and Tatum trying to find ways to spice up their characters marriage. At one point they decided to switch gender roles. We really loved seeing Channing Tatum girling it up a bit and it got all of us talking and recalling some of our earliest memories of crossdressing in music videos. After some reminiscing, we came up with a short list of our favorite music videos that feature crossdressers and the LGBT community.

Here are our Top 5 picks:

Really Don’t Care by Demi Lovato

I Want to Break Free by Queen

We Exist by Arcade Fire

True Trans Soul Rebel by Laura Jane Grace and Miley Cyrus

Super Model by RuPaul

#5 – Really Don’t Care by Demi Lovato

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Shot during the Gay Pride Festival in Los Angeles, Demi Lovato’s hit single was originally written as a breakup song, but it wound up taking on a whole other meaning. When asked about it, Lovato was quoted as saying, “When I sing it, I always want to inspire and empower. I thought what other people could relate to really not caring what people think. I thought of bullies and the LGBT community who are constantly scrutinized. What better place is there than L.A. Pride to celebrate who you are and not really caring what people think?”
The song has become so beloved by the Trans and Crossdresser community that it was featured on an episode of RuPaul’s Drag Race and has over 192 million views on YouTube.

#4 – I Want to Break Free by Queen

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There is no other frontman in music history quite like Freddie Mercury and rightfully so. With Queen’s I Want to Break Free, Mercury switched to full girl mode with his iconic mustache and leather mini skirt to boot, vacuuming the living room while singing this song. The rest of the band follow suit dressing up as a grandma and a school girl, with Brain May taking things a little further with his hair in curlers while in a nightgown. The song is an anthem for all of us girls who are looking to break free and show off our femme selves to the world.

#3 – We Exist by Arcade Fire

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Probably the most controversial video on the list, We Exist by Arcade Fire definitely made a statement upon its release in 2014. Some in the Trans community were offended by the casting of Andrew Garfield as the main character instead of using a true transgender actor in the role. Lead singer Win Butler defended his choice by stating, “pretty damn powerful … for a gay kid in Jamaica to see the actor who played Spider-Man in that [part].” But one look at Garfields commitment to the role and you can see that he was a great choice to play the part.
One defender was transgender musician Lady J (who coached Garfield) saying, “Andrew & I saw the character as a young man who is exploring his gender, not [as] a realized trans woman.” We Exist is very powerful in its message of acceptance; whether it be a trans kid trying to find his way in the world or a gay person hoping for the approval of friends and family. Many critics were eventually won over after seeing the video and its message for what it truly is and hopefully Arcade Fire’s message can be heard for many years to come.

#2 – True Trans Soul Rebel by Laura Jane Grace and Miley Cyrus

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One of those people who originally spoke out against the Arcade Fire video was Against Me frontwoman Laura Jane Grace (who has since retracted her comments). Grace was born Thomas James Gabel, Grace had dealt with gender dysphoria since childhood, finally coming out as a transgender woman in 2012. The rock community has embraced Grace’s coming out and her band are still touring and rocking out with their fans all over the world. This great little acoustic punk song in the vein of Springsteen is a crowd favorite as the band plays it live quite often.
When Rolling Stone asked Grace about her inspiration for the song, she said, “You become more brave about presenting femme, but you’re still closeted, so you have nowhere to go… You end up in a weird motel in the middle of nowhere, wandering down halls, hoping nobody sees you.”
That is something many CD and Trans girls deal with and it’s a great feeling to have songs like this to relate to and inspire us.

#1 – SuperModel by RuPaul

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How could any other song top our list? RuPaul truly brought crossdressing to the masses with this surprise hit in an era when grunge was ruling the airwaves. It was the first time that a hit video featuring a drag queen was featured so prominently and showed the world it was ok to get glamorous no matter what your gender. Ever since SuperModel, RuPaul has launched an amazing career that has spawned into one of our favorite shows, RuPauls Drag Race amongst so much more. RuPaul has done so much for our community over the last 25 years that our favorite drag queen will always be our #1.

Let us know what some of your favorite music videos featuring crossdressing are. Post some links to our Facebook page. If you see any outfits or looks in these videos that you are looking to replicate, check out our store https://www.glamourboutique.com/ or give us a call for some help. If you would liek to read some more articles and are looking for some tips on crossdressing, be sure to visit our blog https://www.glamourboutique.com/crossdressingtipsblog.